Process of making synthetic resin adhesive base from cresylic acid and furfural



UNITED STATES PATENT OFFICE PROCESS OF MAKING SYNTHETIC RESIN ADHESIVEBASE FROM CRESYLIC ACID AND FURFURAL Donald V. Redfern, Seattle, Wash.,assignor, by mesne assignments, to American-Marietta Company, Chicago,Ill., a corporation of Illinois No Drawing. Application September 8,1942, Serial No. 457,650

. 1 Claim. (Cl. 260-7) l 2 This invention relates to the manufacture ofa and furfural in a molar ratio of about two mols synthetic resinousproduct suitable for use as a of cresylic acid to one mol of furfuraltogether glue base. The resin comprises the reaction with a substantialamount of the modifying agent. product of a phenol and/or its homologswith an Among the suitable modifying agents, the followaldehyde and amodifying material in an alkaline ing may be mentioned: so-calledinsoluble blood, medium, the whole being absorbed by another driedactivated sludge, or sulfur. These matematerial, which may be termed anabsorbent. rials are refluxed in order to form a resin which, Theproduct when cooled is ahard, comminutable before or after the additionof the "absorbent substance. material, will form a product which hardensat The phenols and aldehydes selected are of such 10 about -C. in thepresence of an alkaline cataa nature as to form a resin in the absenceof lyst such as caustic soda in the amount of about water, except forthe limited quantity of water ten per cent (10%) figured on the basis ofthe which serves as the solvent for the catalyst, and furfural added.Suflicient absorbent material,

the water of condensation formed in the reaction. such as activatedsludge and/ or insoluble blood, The material thus formed is hydrophobicin char- 15 are added to make the resin easily comminutable. acter, thewater being removed during the re- This resin is made in a kettle with areflux conaction period. This procedure results in a resin denser soarranged that the water dispelled can that is dry when brought to thecompletion stage be run ofi, whereas any of the cresylic acid or sincewater of condensation/is continuously refurfural that comes off can bereturned to the moved, as it is formed, from the reaction vessel. :0reaction chamber. The resin so formed is suit- Heretofore most of theresinous plywood glue able as a base for plywood glues, which arewateradh-esive bases have been formed in the presence proof and willpass the standard tests for exterior of a considerable quantity ofWater, this water moisture-resistance requirements as set iorth inhaving to be removed later through some sort of the National Bureau ofStandards Commercial drying process, or the resin applied in a liquidStandard Bulletin Numbered 0545-38 (a U. S. form. These prior liquidresins, after being Department of Commerce publication). made, are hardto transport, have a short life due I do not wish to confine myself toany specific to the continued condensation, and necessitate grade ofcresylic acidin the manufacture of the the shipping of a large quantityof water at a above-described resin, although it has been foundrelatively high cost. that any grade or combination thereof imparts Myinvention, on the other hand, relates to the spe fi y difierentcharacteristics o the finformation of a so-called dry resin, which doesished product. Any alkaline catalyst may be not have to undergo anydrying process in its used, for example sodium and pot sshydroxmanufacture, and which may be readily ground ide, or any of theso-called alkali metal salts, to a line powder at room temperatures, andhas. singly or in combination. However, I prefer to much broader limitson its life because it is in a use sodium hydroxide. dry form and may bestored for an indefinite During the present emergency it is imperativelength of time. that all so-called defense materials be saved Themodifying material is initially included or made to serve their maximumpu p The with the ingredients to be reacted in order to resin adhesivebase described herein can be exproduce a resin which is potentiallythermosettended by materials heretofore thought unsuitting and alkalinedispersible. The absorbing maable for plywood adhesive formulation dueto the terial is added later to the hot resin at the end treatmentundergone in their o m t on. mo of-the initial reaction period in orderto produce these may be mentioned insoluble blood, which a resincomminutable at room temperatures. is known commercially as fertilizerblood and From the mixer in which the absorbent material which has beenheated at high temperature in is added the resin is allowed to flow intopans or its drying p e and activated Sludge, Which is some other similarreceptacle to cool, or it may dried activated sewage sludge that hasundergone be cooled in any other suitable manner. The drastic treatmentto dry it and completely depreferred resin is one made from a cresylicacid 59 stroy all bacteria. The preferred dried activated ace-1,400

resin-forming materials it is possible by my in-,

vention to produce a much greater amount of adhesive base, by theaddition of said extenders," than is achieved with the resin adhesivebases now used by the plywood industry for a similar purpose. Aside fromthe matter of "defense there is here a pronounced economic saving inthat a relatively small amount of the more expensive phenol and aldehydeis made to do the work of a relatively large amount of said materialswhich are being used at the present time.

Resins heretofore used in the manufacture of plywood adhesives haverequired special equipment or special attention when mixed and appliedto the panels. The present resin adhesive base is used in a mannerwholly familiar to, and commonly practiced by, the plywood industry,

. and does not necessitate the use of unfamiliar techniques or addedequipment for its application.

The modifying materials and absorbing materials which have been foundsuitable for my process are the following:

1. Sulfur 2. Proteinous materials, such as: Dried activated sludgeInsoluble blood Soluble blood Casein Oleaginous seed meals, as such,heat-treated, or aldehyde-treated; examples of which are: y PeanutCottonseed Fiaxseed 3. Ligneous materials, such as:

Lignin from sulfite waste liquor Meadol (an alkaline soluble ligninproduct made by the Mead Corporation) 4. Cellulosic materials, such aswood flour 5. Starch containing materials, such as:

Manioc Wheat flour The above materials may be used singly or incombination as modifying materials or as absorbents. They may bereferred to collectively as extenders, by which term either modifyingagents or absorbents or both are intended to be included.

By "modifying agents" as used in the present description and claim, Irefer to materials from the above list which, when added to the reactingingredients before or during the reaction, serve process: I have foundthat the ingredients. temperatures, and proportions stated are welladapted for this purpose and give excellent results, but

it is to be understood that they may be varied to some extent, partlydepending on the type of cresylic acid used and the modifyingagentvemployed. The type of modifying and/or absorbing materials usedalso plays a part in determination of the final quality of the product.

The above named materials are put in a reaction kettle fitted with areflux condenserso that the water formed during the reaction period maybe eliminated and any of the furfural or cresylic acid that may becarried over through the condenser and formed in a layer below the waterto be eliminated, may be returned to the reaction kettle. The abovenamed materials are heated to melt the sulfur herein used as themodifying agent, the caustic soda solution is then added and themixtureboiled for twenty-five (25) minutes. One hundred parts ofinsoluble blood (absorbing material) are then addedand mixed inthoroughly and the resultant resin is poured on to trays to cool. Aftercooling the resin is ground to pass at least a one hundred-mesh (100)screen. This base is now suitable for admixture, in varying proportionsdependent upon the quality of adhesive desired, withalkaline-dispersible material to form a new and superior type of piywoodadhesive, as set forth in my application Serial No. 467,909, fliedDecember 4, 1942.

Example No. .2

This is the same as Example No. 1 except that one hundred (100) parts ofactivated sludge is used to absorb the resin in place of the insolubleblood.

The proportions of resin-forming material used and the proportions andkind of extenders determine the kind of resin adhesive base formed. Thisbase may be used to form adhesives which in turn are used to glueplywood panels which range in moisture resistance requirements from thehighly water resistant exterior type down to the moderately waterresistant interior type as determined in tests set forth by the NationalBureau of Standards (see above bulletin reference).

The final product of the present application may be termed a "resinbase" and may be used as one of the ingredients in the resin baseadhesive as set forth in my application Serial No. 467,909, filed Dec.4,1942, entitled Synthetic resin base adhesive and method of making same,now Patent No. 2,430,736.

I claim:

A process which comprises reacting together cresylic acid, furfural anda modifying agent comprising sulphur at an elevated temperature in thepresence of an alkaline catalyst to produce an alkaline dispersiblepotentially thermosetting resin, adding to the resin an absorbingmaterial comprising insoluble blood, intimately mixing the mass and thencooling, thereby producing a hard,

coniminutable substance suitable for use as an on following page)REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS 5 Number Name Date 1,771,033 Ellis July 22, 19301,771,553 Arnot July 29, 1930 1,877,202 Satow Sept. 13, 1932 101,884,747 Knapp Oct. 25, 1932 1,988,475 Berlin Jan. 22, 1935 NumberNumber

